2-(ortho-phenylbenzyl) imidazoline and acid addition salts



United States Patent Z-(ORTHO-PHENYLBENZYL) IMIDAZOLINE AND ACIDADDITION SALTS Merrill Eugene Specter, Kalamazoo, Mich., assignor toBristol Laboratories Inc., Syracuse, N. Y., a corporation of New York NoDrawing. Application June 27, 1955, Serial No. 518,351

3 Claims. (Cl. 2603l 9.6)

where R is phenyl.

The acid addition salts of this compound are also included within thepresent invention. Some examples of the nontoxic acid addition salts ofthe free base with inorganic or organic acids which may be prepared bythe methods hereinafter described are the hydrochloride, hydrobromide,hydroiodide, sulfate, phosphate, maleate, acetate, citrate, oxalate,succinate, benzoate, tartrate, and the like.

The compounds of this invention are also useful for their ability toincrease blood pressure.

. solid was distilled under reduced pressure.

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The following example will serve to illustrate the invention withoutlimiting it thereto.

Example Z-(ortho-phenylbenzyl)-imidazoline is prepared by heating 30grams (0.124 mole) of ethyl ortho-biphenyl-acetate and 22.3 grams (0.37mole) of ethylenediamine in a pressure bottle on a steambath forforty-eight hours. Upon standing several hours, a solid separated fromthe reaction mixture which was filtered and recrystallized from aceticacid. The solid melted at 214216 C. and was insoluble in dilutehydrochloric acid. The filtrate from the A fraction which had a boilingpoint of 196-200 C. at 4.5 mm. was obtained which crystallized. Thesolid was recrystallized first from cyclohexane and then from methylisobutyl ketone to obtain a crystalline product having a melting pointof l 12-l 13 C., the yield thereof being 8 grams. The acid addition saltof the free base may be prepared by dissolving it in isopropyl alcoholand saturating this solution with dry hydrogen chloride in the cold. Thecrystalline hydrogen chloride, which forms and slowly separates, iscollected by filtration.

Analysis.-Calculated for CmHrsNa-HCI:

Calculated Found I claim:

No references cited.

1. A COMPOUND SELECTED FROM THE GROUP CONSISTING OF2-(ORTHO-PHENYLBENZYL)-IMIDAZOLINE AND ACID ADDITION SALTS THEREOF.